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Details

Stereochemistry ACHIRAL
Molecular Formula C19H19ClN2.C6H6O7.2Na
Molecular Weight 546.908
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESLORATADINE CITRATE DISODIUM

SMILES

[Na+].[Na+].OC(=O)C(O)(CC([O-])=O)CC([O-])=O.ClC1=CC2=C(C=C1)C(=C3CCNCC3)C4=C(CC2)C=CC=N4

InChI

InChIKey=RDLARMRWOHXAFV-UHFFFAOYSA-L
InChI=1S/C19H19ClN2.C6H8O7.2Na/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13;7-3(8)1-6(13,5(11)12)2-4(9)10;;/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;/q;;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H19ClN2
Molecular Weight 310.821
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H6O7
Molecular Weight 190.1076
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021165s017,021300s014,021312s015,021563s003lbl.pdf

Desloratadine is an active, descarboethoxy metabolite of loratadine. It acts by selective inhibition of H1 histamine receptor and thus provides relief to patients with allergic rhinitis and chronic idiopathic urticaria. Desloratadine was approved by FDA and it is currently marketed under the name Clarinex (among the others).

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
Palliative
CLARINEX

Approved Use

Desloratadine Tablets are indicated for: Seasonal Allergic Rhinitis, Perennial Allergic Rhinitis, Chronic Idiopathic Urticaria.

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
56.9 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
84.5%
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DESLORATADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
Disc. AE: Somnolence, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Somnolence (1 patient)
Abdominal pain (1 patient)
Sources: Page: p. 25
45 mg 1 times / day multiple, oral
Highest studied dose
Dose: 45 mg, 1 times / day
Route: oral
Route: multiple
Dose: 45 mg, 1 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 1 patient
Disc. AE
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
Somnolence 1 patient
Disc. AE
1.25 mg 1 times / day steady, oral
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources: Page: p. 25
unhealthy, 2-11 years
n = 48
Health Status: unhealthy
Age Group: 2-11 years
Sex: M+F
Population Size: 48
Sources: Page: p. 25
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
not significant [IC50 43 uM]
strong [Ki 1.3 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
weak [Inhibition 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
likely
no (pharmacogenomic study)
Comment: pharmacogenotype 2C19 does not correlate with systemic exposure
Page: 19.0
likely
no (pharmacogenomic study)
Comment: lack of correlation in between 2D6 genotype and 3-OH DCL formation
Page: 10.0
likely
weak (co-administration study)
Comment: Coadministration of ketonconazole, mean drug Cmax and AUC0-24 values at steady state were increased by 29-45% and 21-39%, respectively; Coadministration with erythromycin, mean drug Cmax and AUC 0-24 at steady state were increased by 24% and 14%, respectively.
Page: 10.0
yes
yes
weak (co-administration study)
Comment: Coadministration of ketonconazole, mean drug Cmax and AUC0-24 values at steady state were increased by 29-45% and 21-39%, respectively; Coadministration with erythromycin, mean drug Cmax and AUC 0-24 at steady state were increased by 24% and 14%, respectively.
Tox targets
PubMed

PubMed

TitleDatePubMed
[The effect of second generation histamine antagonists on the heart].
2001
Desloratadine.
2001
The pharmacologic profile of desloratadine: a review.
2001
Sensitive liquid chromatography-tandem mass spectrometry method for the determination of loratadine and its major active metabolite descarboethoxyloratadine in human plasma.
2001 Apr 20
[A new antihistamine. Inhibiting inflammation in rhinorrhea and nasal congestion].
2001 Apr 5
Effect of desloratadine and loratadine on rhinovirus-induced intercellular adhesion molecule 1 upregulation and promoter activation in respiratory epithelial cells.
2001 Aug
Pharmacology and clinical efficacy of desloratadine as an anti-allergic and anti-inflammatory drug.
2001 Mar
Pharmacokinetic and safety profile of desloratadine and fexofenadine when coadministered with azithromycin: a randomized, placebo-controlled, parallel-group study.
2001 Mar
Desloratadine reduces nasal congestion in patients with intermittent allergic rhinitis.
2001 Nov
In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes.
2001 Sep
Second-generation antihistamines in asthma therapy: is there a protective effect?
2002
Poor sleep and daytime somnolence in allergic rhinitis: significance of nasal congestion.
2002
Advances in allergy management.
2002
Impact and modulation of nasal obstruction.
2002
Chronic urticaria: impact of allergic inflammation.
2002
Therapeutic points of intervention and clinical implications: role of desloratadine.
2002
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays.
2002
Lack of clinically relevant interaction between desloratadine and erythromycin.
2002
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.
2002 Aug 9
[The place of new antihistamines in allergy management. Apropos of desloratadine].
2002 Dec
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
Treatment of allergic rhinitis.
2002 Dec 16
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
Effect of desloratadine versus placebo on nasal airflow and subjective measures of nasal obstruction in subjects with grass pollen-induced allergic rhinitis in an allergen-exposure unit.
2002 Jun
Desloratadine (Clarinex).
2002 Mar 18
Gateways to clinical trials.
2002 May
Desloratidine for the treatment of chronic urticaria.
2002 Oct
Effects of fexofenadine and desloratadine on subjective and objective measures of nasal congestion in seasonal allergic rhinitis.
2002 Oct
Severe hepatotoxicity after application of desloratadine and fluconazole.
2003
Desloratadine: an update of its efficacy in the management of allergic disorders.
2003
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
Efficacy and safety of desloratadine 5 mg once daily in the treatment of chronic idiopathic urticaria: a double-blind, randomized, placebo-controlled trial.
2003 Apr
Efficacy of azelastine nasal spray in patients with an unsatisfactory response to loratadine.
2003 Aug
Studies on performance and sleepiness with the H1-antihistamine, desloratadine.
2003 Aug
Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine.
2003 Aug 13
Interactions of olopatadine and selected antihistamines with model and natural membranes.
2003 Dec
Comparative in vivo bioactivity of modern H1-antihistamines on AMP challenge in atopic asthma.
2003 Feb
Desloratadine: a nonsedating antihistamine.
2003 Feb
Comparison of ketotifen fumarate ophthalmic solution alone, desloratadine alone, and their combination for inhibition of the signs and symptoms of seasonal allergic rhinoconjunctivitis in the conjunctival allergen challenge model: a double-masked, placebo- and active-controlled trial.
2003 Jul
Desloratadine inhibits allergen-induced airway inflammation and bronchial hyperresponsiveness and alters T-cell responses in murine models of asthma.
2003 Jul
The effects of histamine and leukotriene receptor antagonism on nasal mannitol challenge in allergic rhinitis.
2003 Jun
Gateways to clinical trials. March 2003.
2003 Mar
Decongestant effects of antihistamines: a class effect?
2003 Mar
Efficacy and safety of desloratadine in the treatment of perennial allergic rhinitis.
2003 Mar
[Multicenter study of the effectiveness and tolerability of desloratadine in seasonal allergic rhinitis].
2003 May 25
Desloratadine for allergic rhinitis.
2003 Nov 15
Twenty-four-hour activity and consistency of activity of levocetirizine and desloratadine in the skin.
2003 Oct
[Modern antihistaminics against allergic rhinitis. Better breathing without side effects].
2003 Oct 30
Improvements in simulated real-world relevant performance for patients with seasonal allergic rhinitis: impact of desloratadine.
2004 Apr
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research.
2004 Jan
Patents

Sample Use Guides

Adults and Adolescents 12 Years of Age and Over: take 5 mg tablet once daily. Children 6 to Years of Age: take 2.5 mg tablet once daily. Children 12 Months to 5 Years of Age: take 1.25 mg tablet once daily. Children 6 to 11 Months of Age: 1 mg tablet once daily.
Route of Administration: Oral
In Vitro Use Guide
Nasal epithelial cells (activated by 1 uM of histamine) were treated with 10 uM of desloratadine and the inhibitory activity of the drug on expression of ICAM-1 and HLA-DR was studied.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:17:15 GMT 2023
Edited
by admin
on Sat Dec 16 18:17:15 GMT 2023
Record UNII
CZ422FA2AK
Record Status Validated (UNII)
Record Version
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Name Type Language
DESLORATADINE CITRATE DISODIUM
Common Name English
1,2,3-PROPANETRICARBOXYLIC ACID, 2-HYDROXY-, SODIUM SALT, COMPD. WITH 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDINYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE (1:2:1)
Systematic Name English
Desloratadine citrate disodium [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
CZ422FA2AK
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
CAS
1602766-05-1
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
SMS_ID
100000164231
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
PUBCHEM
163203578
Created by admin on Sat Dec 16 18:17:16 GMT 2023 , Edited by admin on Sat Dec 16 18:17:16 GMT 2023
PRIMARY
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